EP1976899B1 - Härtbare zusammensetzung - Google Patents

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Publication number
EP1976899B1
EP1976899B1 EP07704089.7A EP07704089A EP1976899B1 EP 1976899 B1 EP1976899 B1 EP 1976899B1 EP 07704089 A EP07704089 A EP 07704089A EP 1976899 B1 EP1976899 B1 EP 1976899B1
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Prior art keywords
composition according
mono
diglycidylether
bisphenol
adduct
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French (fr)
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EP1976899B8 (de
EP1976899A1 (de
Inventor
Isabelle Marie Marguerite Muller-Frischinger
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Huntsman Advanced Materials Licensing Switzerland GmbH
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Huntsman Advanced Materials Switzerland GmbH
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/182—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing using pre-adducts of epoxy compounds with curing agents
    • C08G59/184—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing using pre-adducts of epoxy compounds with curing agents with amines
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
    • C08G59/50—Amines
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
    • C08G59/62—Alcohols or phenols

Definitions

  • the polyamines used according to this invention are aliphatic, cycloaliphatic or araliphatic amines like for example: 1,2-diaminoethane (ethylenediamine (EDA)); 1,2-propanediamine; 1,3-propanediamine; 1,4-diaminobutane; 2,2-dimethyl-1,3-propanediamine (neopentanediamine); diethylaminopropylamine (DEAPA); 2-methyl-1,5-diaminopentane; 1,3-diaminopentane; 2,2,4-Trimethyl-1,6-diaminohexane or 2,4,4-Trimethyl-1,6-diaminohexane and mixtures thereof (TMD); 1-amino-3-aminomethyl-3,5,5-trimethylcyclohexane; 1,3-bis(aminomethyl)-cyclohexane; 1,2-bis(aminomethyl)cyclohexane; hexamethylene
  • polyamines are 1,14-diamino-4 11-dioxatetradecane; dipropylenetriamine; 2-methyl-1,5-pentanediamine; N,N'-dicyclohexyl-1,6-hexanediamine; N,N'-dimethyl-1,3-diaminopropane; N,N'-diethyl-1,3-diaminopropane; N,N-dimethyl-1,3-diaminopropane; secondary pofyoxypropylenedi- and triamine; 2,5-diamino-2,5-dimethylhexane; bis-(amino-methyl)tricyclopentadiene; 1,8-Diamino-p-menthane; Bis-(4-amino-3,5-dimethylcyclohexyl)methane; 1,3-Bis(aminomethyl)cyclohexane (1,3-BAC); dipentylamine N-2-(amin
  • the polyamine of component b1b) or b2) is selected from ni-xylylenediamine, isophoronediamine, trimethylehexamethylenediamine, 1,2-diaminocyclohexane; 1,3-bis(aminomethyl)-cyclohexane, diethylenetetriamine, diaminodicyclohexylmethane:
  • the polyphenol novolac is a homopolymer resulting from the condensation of a phenolic compound of formula (I) or (II) with formaldehyde (paraformaldehyde) or a copolymer of different phenolic compounds of formula (I) and/or (II) with formaldehyde (paraformaldehyde): wherein in formula (I) and (II) R 1 , R 2 , R 3 , R 4 , independently of one another are H, branched or unbranched alkyl radicals containing 1 to 15 carbon atoms, and R 5 , R 6 independently of each other represent H, CH 3 , CF 3 .
  • Preferred novolacs derived from compounds of formula (I) are those, wherein in formula (I) R 1 , R 2 , R 3 , R 4 are either H (phenol), or alkylphenols, wherein, while the remaining radicals R 1 to R 4 are H, one or two of the radicals R 1 to R 4 are the radical -CH 3 , or one of the radicals R 1 to R 4 is a tert-butyl radical, or one of the radicals R 1 to R 4 is a long-chain branched or unbranched alkyl radical containing 8 to 15 carbon atoms.
  • Very preferred novolacs are those derived from compounds of formula (I), and especially preferred novolacs are those derived from phenol.
  • the epoxy resin composition can optionally further include other commonly used additives selected for example from flow control additives, antifoaming agents, anti-sag agents, pigments, reinforcing agents, fillers, elastomers, stabilizers, extenders, plasticizers, flame retardants, accelerators, colorants, fibrous substances, thixotropic agents, and anti-corrosive pigments.
  • flow control additives antifoaming agents, anti-sag agents, pigments, reinforcing agents, fillers, elastomers, stabilizers, extenders, plasticizers, flame retardants, accelerators, colorants, fibrous substances, thixotropic agents, and anti-corrosive pigments.
  • accelerators in catalytic amounts for epoxy/amine reactions can be used in addition to the new curing agents.
  • Suitable examples are for instance Mannich base type accelerators like Accelerators 2950 and 960-1 from Huntsman Advanced Materials, tertiary amines like benzyldimethylamine (BDMA), metal salts like hydroxides and nitrates most known those of group I and group II metals such as calcium, lithium etc. as described in EP 0 083 813 A1 and EP 0 471 988 A1 , or acids like salicylic acid can be, added as well.
  • the amount of accelerator is from 0.1 to 10, preferably from 0.3 to 5, more preferably from 0.5 to 3 % per weight based on the total weight of components b1), b2), b3) and accelerator.
  • Full cure times of the cited examples are equal or less than 10 hours at 5°C and achieved in absence of solvents, and thus being as fast or even faster than cure times obtained by using phenalkamines (alkylated phenolic polyamines), that are known for providing fast cure times at low temperatures with a workable pot life.
  • phenalkamines alkylated phenolic polyamines
  • the isolated adduct A was prepared using following procedure:
  • the isolated adduct D was prepared using following procedure :
  • the isolated adduct E was prepared using following procedure:
  • Persoz hardness was measured on glass sheets coated with the above formulations using a Byk pendulum hardness tester (ISO 1522). The coating thickness measured on glass was between 250-300 microns.
  • Example 2 Cure properties and mechanical properties of hardeners B and C compared to hardener Aradur 943.
  • the cure properties of hardeners B and C were compared to those of Aradur 943 as well using the epoxy resin GY 250..
  • the full cure times of the blend hardeners are somewhat prolonged by the addition of 1,2-diaminocyclohexane and supraplast 3616 compared to the pure isolated adduct A in formulation 1 and compared to Aradur 943.
  • the dust free time here again was reduced by the modification of the system with supraplast 3616 compared to the Aradur 943 and also the viscosity of the formulation is reduced compared to formulation 1 and comparative 1.
  • the hardness increase in function of the time is as good as for Aradur 943 and the isolated adduct A.
  • the coating thickness measured on degreased steel panels was between 250-300 microns.
  • Erichsen indentation test was measured on Erichsen instrumentation, a standard method for measuring the elasticity of film. In this test, a sphere is pressed from the backside against the panel. The level of indentation before cracking is measured in mm (ISO 1520 / DIN 53156).
  • Impact deformation directly impact is determined by dropping a punch having a weight of 2Kg, on the underside of which there is a sphere of 20 mm in diameter, directly onto the coated surface from a certain height, underside down.
  • the coating hardness build up of the three adducts D, E and F is comparable to this of the commercial system Aradur 943, which means that the different systems are curing as fast as Aradur 943 (table 9).
  • the pot lifes of all three adducts D, E and F are surprisingly much longer than this of the commercial Aradur 943 system.
  • the final hardness of the coatings prepared with hardeners adducts E or F based on DY 0397 (butanediol diglycidylether) have the lowest final hardness after two weeks cure at 23°C when compared to Aradur 943 and isolated adduct D.
  • the coatings made with adduct A and blend B show equivalent and good resistance to corrosion and both can be further used in primer formulation for instance for marine and heavy duty application.

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Epoxy Resins (AREA)
  • Paints Or Removers (AREA)
  • Adhesives Or Adhesive Processes (AREA)
  • Compositions Of Macromolecular Compounds (AREA)

Claims (12)

  1. Härtbare Zusammensetzung umfassend
    a) ein Epoxyharz, enthaltend im Mittel mehr als eine Epoxygruppe pro Molekül, und
    b) als Härtungsmittel eine Zusammensetzung umfassend
    b1) 40 bis 80 Gewichts% eines Reaktionsprodukts der Umsetzung von
    b1a) mindestens einem Diglycidyl- und/oder mindestens einem Monoglycidylether mit
    b1b) einer Zusammensetzung umfassend ein flüchtiges Monoamin und ein Polyamin,
    wobei die Zusammensetzung b1b) in einer Menge verwendet wird, so dass ein Überschuss Aminogruppen relativ zu Epoxygruppen aus b1a) erhalten wird, und wobei der Überschuss an Monoamin aus dem Reaktionsprodukt entfernt wird,
    b2) 15 bis 50 Gewichts% Polyamin und
    b3) 5 bis 20 Gewichts% Polyphenol-Novolak,
    und worin die Summe der Komponenten b1), b2) und b3) 100 Gewichts% beträgt.
  2. Zusammensetzung nach Anspruch 1, worin die Komponente a) ausgewählt ist aus Diglycidylether von Bisphenol A, Diglycidylether von Bisphenol F, Mono- oder Diglycidylether von einwertigen oder zweiwertigen zykloaliphatischen Alkoholen, Mono- oder Diglycidylether von einwertigen oder zweiwertigen aliphatischen Alkoholen.
  3. Zusammensetzung nach Anspruch 1 oder 2, worin die Komponente a) mit einem reaktiven Verdünnungsmittel vorgemischt wird.
  4. Zusammensetzung nach einem der Ansprüche 1 bis 3, worin die Komponenten b1a) ausgewählt ist aus Diglycidylether von Bisphenol A, Diglycidylether von Bisphenol F, Polyglycidylether von mehrwertigen Phenol- oder Kresol-Novolaken, Mono- oder Polyglycidylether von einwertigen oder mehrwertigen zykloaliphatischen Alkoholen, Mono- oder Polyglycidylether von einwertigen oder mehrwertigen aliphatischen Alkoholen.
  5. Zusammensetzung nach einem der Ansprüche 1 bis 4, worin das Polyamin der Komponente b1b) oder b2) ausgewählt ist aus m-Xylylendiamin, Isophorondiamin, Trimethylhexamethylendiamin, 1,2-Diaminozyklohexan, 1,3-Bis(aminomethyl)-zyklohexan, Diethylentetriamin, Diaminodizyklohexylmethan.
  6. Zusammensetzung nach einem der Ansprüche 1 bis 5, worin das Polyphenol-Novolak ein Homopolymer ist, welches aus der Kondensation von phenolischen Verbindungen der Formel (I) oder (II) mit Formaldehyd (Paraformaldehyd) oder einem Copolymer von unterschiedlichen phenolischen Verbindungen der Formel (I) und/oder (II) mit Formaldehyd (Paraformaldehyd) resultiert:
    Figure imgb0004
     worin in Formel (I) und (II) R1, R2, R3, R4 unabhängig voneinander H, verzweigte oder unverzweigte Alkylreste mit 1 bis 15 Kohlenstoffatomen sind, und R5, R6 unabhängig voneinander H, CH3, CF3 darstellen.
  7. Zusammensetzung nach einem der Ansprüche 1 bis 6, worin das Polyphenol-Novolak unumgesetzte freie phenolische Verbindungen umfasst, vorzugsweise Verbindungen der Formel (I) und/oder (II), in einer Menge von nicht mehr als 10 Gewichts%, vorzugsweise weniger als 7,5 Gewichts%, am meisten bevorzugt weniger als 5 Gewichts%, basierend auf dem Gesamtgewicht der Härtungsmittelmischung b).
  8. Zusammensetzung nach einem der Ansprüche 1 bis 7, worin die Komponente b1) in Gegenwart eines Lösungsmittels hergestellt ist.
  9. Zusammensetzung nach einem der Ansprüche 1 bis 8, welche zusätzlich anorganische und/oder organische Additive, ausgewählt aus Fließregulieradditiven, Antischaummitteln, Antiabsetzmitteln, Pigmenten, Verstärkern, Füllstoffen, Elastomeren, Stabilisatoren, Streckungsmitteln, Weichmachern, Flammschutzmitteln, Beschleunigern, Farbstoffen, Fasersubstanzen, thixotropen Mitteln, Antikorrosionspigmenten, umfasst.
  10. Zusammensetzung nach Anspruch 9, worin als Additiv Salizylsäure verwendet wird.
  11. Gehärtetes Material, erhalten durch Härten einer Zusammensetzung nach einem der Ansprüche 1 bis 10.
  12. Verwendung einer Zusammensetzung nach einem der Ansprüche 1 bis 10 zur Bereitstellung von Schutzüberzügen und Adhäsiven.
EP07704089.7A 2006-01-24 2007-01-23 Härtbare zusammensetzung Active EP1976899B8 (de)

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PCT/EP2007/050655 WO2007085598A1 (en) 2006-01-24 2007-01-23 Curable composition
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EP (2) EP1810985A1 (de)
JP (1) JP5296551B2 (de)
KR (1) KR101360870B1 (de)
CN (1) CN101374879B (de)
AU (1) AU2007209333A1 (de)
ES (1) ES2611607T3 (de)
WO (1) WO2007085598A1 (de)

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WO2007085598A1 (en) 2007-08-02
CN101374879B (zh) 2011-11-30
EP1810985A1 (de) 2007-07-25
KR101360870B1 (ko) 2014-02-21
JP2009523879A (ja) 2009-06-25
CN101374879A (zh) 2009-02-25
ES2611607T3 (es) 2017-05-09
EP1976899B8 (de) 2017-03-01
KR20080085152A (ko) 2008-09-23
US7786223B2 (en) 2010-08-31
AU2007209333A1 (en) 2007-08-02
US20090036582A1 (en) 2009-02-05
EP1976899A1 (de) 2008-10-08

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